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Prestwick2_001095
Also known as: 512-15-2, Cyclopentylate, Cyclogyl, 2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate, Ciclopentolato, Cyclopentolatum
Molecular Formula
C17H25NO3
Molecular Weight
291.4  g/mol
InChI Key
SKYSRIRYMSLOIN-UHFFFAOYSA-N
FDA UNII
I76F4SHP7J

A parasympatholytic anticholinergic used solely to obtain mydriasis or cycloplegia.
1 2D Structure

Prestwick2_001095

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate
2.1.2 InChI
InChI=1S/C17H25NO3/c1-18(2)12-13-21-16(19)15(14-8-4-3-5-9-14)17(20)10-6-7-11-17/h3-5,8-9,15,20H,6-7,10-13H2,1-2H3
2.1.3 InChI Key
SKYSRIRYMSLOIN-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCOC(=O)C(C1=CC=CC=C1)C2(CCCC2)O
2.2 Other Identifiers
2.2.1 UNII
I76F4SHP7J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cyclogyl

2.3.2 Depositor-Supplied Synonyms

1. 512-15-2

2. Cyclopentylate

3. Cyclogyl

4. 2-(dimethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate

5. Ciclopentolato

6. Cyclopentolatum

7. Cyclopentolatum [inn-latin]

8. Ciclopentolato [inn-spanish]

9. Mydrilate

10. Bell Pentolate

11. Cyclopentolate (inn)

12. 2-(dimethylamino)ethyl 1-hydroxy-alpha-phenylcyclopentaneacetate

13. I76f4shp7j

14. 1-hydroxy-alpha-phenylcyclopentaneacetic Acid 2-(dimethylamino)ethyl Ester

15. Benzeneacetic Acid, .alpha.-(1-hydroxycyclopentyl)-, 2-(dimethylamino)ethyl Ester

16. Chebi:4024

17. 2-(dimethylamino)ethyl (1-hydroxycyclopentyl)(phenyl)acetate

18. Alpha-(1-hydroxycyclopentyl)benzeneacetic Acid 2-(dimethylamino)ethyl Ester

19. Beta-dimethylaminoethyl (1-hydroxycyclopentyl)phenylacetate

20. Tsiklopentolat;cyclogyl;dl-cyclopentolate

21. Cyclopentoiate

22. Diopentolate

23. Beta-(dimethylamino)ethyl (1-hydroxycyclopentyl)phenylacetate

24. 2-phenyl-2-(1-hydroxycyclopentyl)ethanoic Acid Beta-(dimethylamino)ethyl Ester

25. Cyclopentolate [inn]

26. Cyclopentolate [inn:ban]

27. (+-)-cyclopentolate

28. Bell Pentolate (tn)

29. Einecs 208-136-4

30. Unii-i76f4shp7j

31. Cyclo-pentolatum

32. Benzeneacetic Acid, Alpha-(1-hydroxycyclopentyl)-, 2-(dimethylamino)ethyl Ester

33. Cyclogyl (salt/mix)

34. Mydrilate (salt/mix)

35. Spectrum_000856

36. (+/-)-cyclopentolate

37. 2-dimethylaminoethyl 2-(1-hydroxycyclopentyl)-2-phenylacetat

38. Prestwick0_001095

39. Prestwick1_001095

40. Prestwick2_001095

41. Prestwick3_001095

42. Spectrum2_001122

43. Spectrum3_000369

44. Spectrum4_000303

45. Spectrum5_000793

46. Cyclopentolate [mi]

47. Bspbio_001170

48. Bspbio_002097

49. Kbiogr_000886

50. Kbioss_001336

51. Cyclopentolate [vandf]

52. Divk1c_000610

53. Schembl132500

54. Spbio_000983

55. Spbio_003055

56. Bpbio1_001288

57. Gtpl7153

58. Cyclopentolate [who-dd]

59. Chembl1201338

60. Dtxsid3048528

61. Bdbm82375

62. Kbio1_000610

63. Kbio2_001336

64. Kbio2_003904

65. Kbio2_006472

66. Kbio3_001317

67. Ninds_000610

68. Bcp21334

69. Nsc_2905

70. Mfcd00599448

71. Stl430452

72. Akos015962137

73. Db00979

74. Idi1_000610

75. Cyclopentolatum; Cyclogyl; Cyclopentylate

76. Ncgc00018213-02

77. Ac-15991

78. As-16057

79. Cas_512-15-2

80. Sbi-0051324.p003

81. Ab00053445

82. Ft-0624265

83. C06932

84. D07759

85. H10434

86. Ab00053445_12

87. A913427

88. L000802

89. Q867332

90. Brd-a77291778-003-05-5

91. Brd-a77291778-003-15-4

92. .beta.-(dimethylamino)ethyl (1-hydroxycyclopentyl)phenylacetate

93. 2-(dimethylamino)ethyl (1-hydroxycyclopentyl)(phenyl)acetate #

94. 2-dimethylaminoethyl 1-hydroxy-.alpha.-phenylcyclopentaneacetate

95. (+)-alpha-(1-hydroxycyclopentyl)benzeneacetic Acid 2-(dimethylamino)ethyl Ester

96. (?)-alpha-(1-hydroxycyclopentyl)benzeneacetic Acid 2-(dimethylamino)ethyl Ester

97. 1-hydroxy-.alpha.-phenylcyclopentaneacetic Acid, 2-(dimethylamino)ethyl Ester

98. 2-(dimethylamino)ethyl (+/-)-1-hydroxy-.alpha.-phenylcyclopentaneacetate

99. Cyclopentaneacetic Acid, 1-hydroxy-.alpha.-phenyl-, 2-(dimethylamino)ethyl Ester

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 291.4 g/mol
Molecular Formula C17H25NO3
XLogP32.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass291.18344366 g/mol
Monoisotopic Mass291.18344366 g/mol
Topological Polar Surface Area49.8 Ų
Heavy Atom Count21
Formal Charge0
Complexity331
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCyclogyl
PubMed HealthAtropine
Drug ClassesAnesthetic Adjunct, Cholinergic Antagonist, Gastrointestinal Agent, Nerve Gas Antidote, Urinary Antispasmodic
Drug LabelCYCLOGYL (cyclopentolate hydrochloride ophthalmic solution, USP) is an anticholinergic prepared as a sterile, borate buffered, solution for topical ocular use. It is supplied in three strengths. The active ingredient is represented by the structura...
Active IngredientCyclopentolate hydrochloride
Dosage FormSolution/drops
RouteOphthalmic
Strength0.5%; 1%; 2%
Market StatusPrescription
CompanyAlcon; Alcon Labs

2 of 4  
Drug NamePentolair
Active IngredientCyclopentolate hydrochloride
Dosage FormSolution/drops
RouteOphthalmic
Strength1%
Market StatusPrescription
CompanyBausch And Lomb

3 of 4  
Drug NameCyclogyl
PubMed HealthAtropine
Drug ClassesAnesthetic Adjunct, Cholinergic Antagonist, Gastrointestinal Agent, Nerve Gas Antidote, Urinary Antispasmodic
Drug LabelCYCLOGYL (cyclopentolate hydrochloride ophthalmic solution, USP) is an anticholinergic prepared as a sterile, borate buffered, solution for topical ocular use. It is supplied in three strengths. The active ingredient is represented by the structura...
Active IngredientCyclopentolate hydrochloride
Dosage FormSolution/drops
RouteOphthalmic
Strength0.5%; 1%; 2%
Market StatusPrescription
CompanyAlcon; Alcon Labs

4 of 4  
Drug NamePentolair
Active IngredientCyclopentolate hydrochloride
Dosage FormSolution/drops
RouteOphthalmic
Strength1%
Market StatusPrescription
CompanyBausch And Lomb

4.2 Drug Indication

Used mainly to produce mydriasis and cycloplegia for diagnostic purposes.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cyclopentolate is an anti-muscarinic in the same class as atropine and scopolamine. Cyclopentolate blocks the receptors in the muscles of the eye (muscarinic receptors). These receptors are involved controlling the pupil size and the shape of the lens. Cyclopentolate thus induces relaxation of the sphincter of the iris and the ciliary muscles. When applied topically to the eyes, it causes a rapid, intense cycloplegic and mydriatic effect that is maximal in 15 to 60 minutes; recovery usually occurs within 24 hours. The cycloplegic and mydriatic effects are slower in onset and longer in duration in patients who have dark pigmented irises.


5.2 MeSH Pharmacological Classification

Mydriatics

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)


Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)


Parasympatholytics

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)


5.3 ATC Code

S01FA04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


S - Sensory organs

S01 - Ophthalmologicals

S01F - Mydriatics and cycloplegics

S01FA - Anticholinergics

S01FA04 - Cyclopentolate


5.4 Absorption, Distribution and Excretion

Absorption

Absorbed following ophthalmic administration.


5.5 Mechanism of Action

By blocking muscarinic receptors, cyclopentolate produces dilatation of the pupil (mydriasis) and prevents the eye from accommodating for near vision (cycloplegia).


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